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Villa vacation rentals in Montaione

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Popular amenities for Montaione villa rentals

Private villa rentals

Top guest favorite
A spacious bedroom features a four-poster bed draped with soft fabric. Two bedside lamps create gentle illumination. An arched bookshelf filled with books is visible in the background, alongside a cozy seating area with upholstered chairs, highlighting a mix of comfort and elegance.
Villa in Panzano
4.93 out of 5 average rating, 75 reviews

Luxury Villa on Chianti Wine Estate

StevenRating, 5 stars1 month ago
Wonderful stay at the Villa among the vineyards in Panzano. Vicky, the host, is the owner of Le Fonti winery with the villa surrounded by their vineyards and olive groves. The view from the villa is absolutely stunning. The town of Panzano is very cute. We bought groceries at the Coop and made breakfast each morning, gathering in the cozy well equipped kitchen. There is a courtyard immediately outside the doors of the villa with a large table, and again amazing views. Our time in the villa was so relaxing! Though we went to several wineries, a highlight was a very personal tour of the winery, wine making process and wines by Vicky at Le Fonti. She spent time discussing/pouring the different wines, even bringing over the same wine from different years to show us the difference the weather/grape stress influences the final taste. Overall exactly what we wanted from a Tuscan experience and really enriched by an extremely friendly and knowledgeable host.
Top guest favorite
The entrance of Chiesino Dei Vaioni is framed by tall trees, leading up a gravel driveway. The stone structure features an arched entrance, with decorative elements visible above. Surrounding greenery adds to the serene atmosphere of the property, enhancing its secluded setting.
Villa in Pistoia
5 out of 5 average rating, 62 reviews

Church of the Vaioni

KarlRating, 5 stars3 days ago
The renovated church was incredibly interesting and I was fascinated by its long history. The church is nestled within a tranquil olive grove which made it easy to relax and disconnect from the stressors of the big city. Roberto was absolutely incredible and I cannot give higher praise—he is truly the standard when it comes to hosts. He was attentive, responsive to any issues, and helpful to solve any difficulties that we had with travel arrangements. It’s easy to see why this property is in such high demand. It was my first time staying in Tuscany and Roberto’s church is already calling me back for another stay! Most highly recommended.
Top guest favorite
A private pool surrounded by lush greenery and natural stone walls is featured. Comfortable loungers are positioned on a tiled patio, offering a relaxing space under the open sky. Large glass doors lead into the cottage, inviting natural light into the area.
Villa in Gaiole in Chianti
4.93 out of 5 average rating, 27 reviews

Sestuccina

EmmaRating, 5 stars2 weeks ago
We had a lovely stay at this beautiful villa. The photos do not do it justice at all! From the infinity pool overlooking the vineyard to the hot tub with views of a castle, it was stunning and jaw dropping scenery. Brigittia made sure we were prepared to have a great trip - from helping us with reservations and arranging transportation for us with her husband (who was wonderful) she was a fantastic host. We would love to visit again sometime and would recommend for anyone wanting to spend time in the countryside.
Superhost
A private swimming pool is surrounded by a manicured lawn, featuring two lounge chairs with decorative pillows. A gazebo is visible in the background, offering a shaded area. Warm lights illuminate the garden and the villa, creating an inviting evening ambiance.
Villa in Capannori
4.96 out of 5 average rating, 25 reviews

Luxury Tuscany Villa on the hill with private pool

EmmaRating, 5 stars4 weeks ago
We booked this for a girls holiday and we had the best week. We didn’t hire a car, we walked to a few of neighbouring towns and got a taxi to Lucca, and a train to Florence one day. Neighbouring towns have small supermarkets and the walks to them were enjoyable, the scenery is truly incredible. Lucca is beautiful and has incredible markets, it’s a must see if you stay here. The villa itself is exactly as shown in the pictures, the pool area is gorgeous, we sat around the table every night for dinner, and when it’s dark there’s clusters of fireflies sparkling in the roses, it was magical. Stefania was great, very responsive and there if we needed her. We’d definitely recommend and book this villa again in the future!
Top guest favorite
An infinity pool sits on a green terrace, surrounded by lush greenery and olive groves. Several loungers are positioned on the lawn, offering views of the expansive valley and distant hills under a clear blue sky.
Villa in Loro Ciuffenna
4.98 out of 5 average rating, 51 reviews

The Lazy Oak

JordanRating, 5 stars1 week ago
The Lazy Oak Villa is everything we dreamed of and more for our honeymoon. The house is beautiful, well furnished and feels so homely and comfortable. The surroundings are simply stunning; the view from the house and pool never get old! Mario and Alessandro were super helpful, offering to help us book restaurants and vineyards if needed. Mario keeps to himself so still feels very private but is happy to help with anything and it was nice to see him around (with his cute little dog!) and know he was about if we needed anything. Couldn’t recommend the Lazy Oak Villa more, and we’re already talking about when we could come back!! Thank you Mario and Alessandro!
Guest favorite
A rustic Tuscan farmhouse, restored with care, features a tall tower and expansive windows. Surrounding greenery includes cypress trees and shrubs, complementing the natural landscape. The lawn offers open space for relaxation, enhancing the serene atmosphere of the property.
Villa in Buonconvento
5 out of 5 average rating, 11 reviews

Beautiful tuscan country house

LukasRating, 5 stars1 month ago
The house is beautiful and very big. It is located just outside of Buonconvento and offers complete privacy. A car is an advantage. The rooms are spacious, there are mosquito nets above all beds and enough bathrooms and toilets for everyone. In general, the house is very well equipped, both in the kitchen and otherwise. The pool is slightly elevated, beautiful, large, with natural shade all around and offers a magnificent view on the surrounding countryside. In the huge garden you can eat, linger, play... There is even a small basketball court. But beware: right next door there are wild blackberries and the ball can be lost :) In Buonconvento there is a coop, a fine gelateria and a good coffee with the famous and fine products of Le Dolcezze di Nanni. For a good pizza, the drive to the Mulinum restaurant is worth it a little outside, they have their own mill and process their own grain. We highly recommend the house.
Guest favorite
A panoramic view captures rolling hills adorned with olive groves, overlooking a tranquil pool area. A shaded gazebo rests beside the pool, while cypress trees gently rise in the background. The landscape is rich with greenery, offering a serene escape amidst nature.
Villa in Buti
4.96 out of 5 average rating, 46 reviews

Villa sii felice

KristinRating, 5 stars6 days ago
We had an unforgettable stay at this villa for our bachelorette getaway! The host was incredibly responsive and made everything smooth from start to finish. The views were absolutely breathtaking — even better than in the pictures! The villa had everything we needed to set the perfect atmosphere: fully stocked kitchen with plates and glasses, plenty of towels, and thoughtful details throughout. We loved picking fresh lemons from the garden and finding peaceful spots around the property to read and relax. It’s incredibly private and serene — the perfect escape. While the drive-up can be a bit tricky at first, it quickly becomes second nature and is well worth it.This place exceeded all of our expectations. Highly, highly recommend — we'd come back in a heartbeat!
Superhost
A private swimming pool is surrounded by lush greenery, featuring clear, shimmering water under a partly cloudy sky. The pool area offers expansive views of the surrounding vineyards and olive groves, creating a serene environment for relaxation.
Villa in Castelfiorentino
4.93 out of 5 average rating, 72 reviews

Panoramic" Casa Gello" with private pool.

SarahRating, 5 stars2 weeks ago
We've just arrived back in England after a lovely May half-term week at Monica's house - around 50 mins drive from Pisa airport. We are a family of four, so the kids shared the second bedroom and there was more than sufficient living space. The gardens are beautiful, pool clean and stylish and views amazing at the top of a hill. The air con was welcome as the weather hotted up and great selection of DVDs were very useful in the evenings. We were able to visit Florence, Siena and San Gimignano easily in our hire car. With local restaurants and supermarkets a short drive away, the house remained close enough to everything we needed yet far enough away from any town for it to give us the rest and peace we needed. Thank you Monica for sharing your home with us and the great recommendations and contact - we will definitely try to book again for any other trip to Tuscany.

Luxury villa rentals

Top guest favorite
Bright pink flowers frame a tranquil infinity pool, with rolling green hills visible in the background. The landscape is dotted with tall trees and stretches toward distant mountains under a clear blue sky.
Villa in Barberino Tavarnelle
5 out of 5 average rating, 36 reviews

Valluccia 51

FlorisRating, 5 stars1 month ago
We had an amazing time in the villa from Tommaso. It has all the amenities that you expect from a villa in this price class. The view looking over the valley is beautiful. The communication with the host was very pleasant and swift. As an example; The existing tv got broken in the evening and the next morning Tomasso installed a new one with all the modern features like Apple Airplay. Since the weather was not great the first days you can imagine that this was very nice to have a good working tv. Anyone who is considering renting a villa in the surrounding of San Donato, I highly recommend this villa from Tommaso.
Top guest favorite
An aerial view captures the villa and its surrounding gardens, showcasing well-maintained landscapes, lush greenery, and a private swimming pool. The rustic stone building features a terracotta roof and is complemented by a pergola and a gazebo, all set against a backdrop of rolling hills.
Villa in San Gimignano
4.97 out of 5 average rating, 67 reviews

Truly Tuscan villa with pool 6km to San Gimignano

MikeRating, 5 stars3 weeks ago
As soon as you get out of the car we smelled jasmine. The grounds are so well attended to. Beautiful roses, rosemary bushes everywhere! The pool is much larger than the pictures appear. The views are incredible!! It was the perfect place for us and our adult children with significant others. Our daughters boyfriends family joined us from Great Britain and our other daughter got engaged during our vacation in the backyard of the villa at twighlight. We will never forget this place and the very many memories that it provided. The villa was so comfortable with all the amenities. We were cooking outside and relaxing by the pool daily. Giulia provided a special wine tasting recommendation day of arrival and we also enjoyed our favorite wine tasting right down the road at Corbucci. Do not miss this whatever you do!! Many wonderful days exploring Chianti country also Florence and Sienna close by. Thanks for the BEST holiday ❤️🍷❤️ thank you for making us so comfortable !!
Top guest favorite
A private heated pool is set against a backdrop of a stone and pink exterior villa. Comfortable lounge chairs are positioned nearby, with a small table displaying refreshing drinks. Lush greenery surrounds the area, creating a serene outdoor space with shade from a large canopy.
Villa in Montecatini Terme
5 out of 5 average rating, 40 reviews

Villa Le Panteraie - located between Florence and Pisa

TomRating, 5 stars2 weeks ago
A beautiful villa with exceptional views to the hills and valley. Various oudoor areas. Private location however close to sights and amenities. Cafes and restaurants not far however not walking distance, best accessed by own car. Electric bikes were available for sightseeing. Fantastic host, always responsive and helpful. Can warmly recommend.
Superhost
A panoramic view of a pool set within a serene garden, featuring blooming flowers in the foreground. Olive trees are visible in the background, enhancing the natural beauty of the landscape. The clear blue water of the pool reflects the surrounding greenery.
Villa in Greve in Chianti
4.84 out of 5 average rating, 32 reviews

Romantic Villa with private pool and fabulous view

ReubenRating, 5 stars6 days ago
Most beautiful villa with so much charm! Fantastic location as well, easy to explore Florence, Siena, San Gimignano, as well as all the surrounding wineries and countryside. The villa was so lovely that we decided to spend 2 days in the villa, chilling at the pool drinking wine and having tapas! Janine is a great host with many recommendations of what to do in the local area. Highly recommended to stay here to experience Tuscany!
Superhost
A charming outdoor dining area is presented, featuring a round table surrounded by four wicker chairs with red cushions. A gentle sunset casts a warm glow, while the distant silhouette of San Gimignano towers over the lush green landscape in the background.
Villa in San Gimignano
4.79 out of 5 average rating, 19 reviews

Exclusive Farmhouse Pool & View of San Gimignano

AlineRating, 5 stars1 month ago
This property exceeded our expectations with spectacular views and peaceful, natural surroundings! The host was friendly and responsive. The proximity to San Gimignano and other Tuscan destinations was convenient. Each day felt magical! Just sitting on the patio was amazing! An unforgettable destination and experience!
Guest favorite
A private swimming pool is surrounded by a well-maintained patio area, featuring several loungers and sunshades. Lush greenery borders the space, providing a serene backdrop of typical Tuscan hills under a clear sky.
Villa in Montefoscoli
4.97 out of 5 average rating, 65 reviews

Old renovated mill in the Tuscan hills

StephanRating, 5 stars8 months ago
You can stop looking now! This is probably the most perfect place to stay and with the best host in all of Tuscany. This is said by a very travel and quite picky family from Sweden that this time went with three sons 16, 18 and 22 and the eldest son's fiancée. The host Lorenzo is absolutely amazing both before and during the stay: quick responses, incredibly helpful and very accommodating. You live in a renovated mill (two super-fresh separate buildings one of which is newly built) in the small village of Montefoscoli, with wonderful views of the landscape and sun location from morning till night. Large patio with barbecue and pool for lovely meals and relaxing. Inside there is everything you need and more: full equipped kitchen, dishwasher, washing machine, ironing equipment, ac in each bedroom. Good wifi and TV box. Excellent little bakery 50 meters from the residence. A small Coop shop 5 minutes walking distance from the residence with everything you need. We've already told friends and acquaintances about this home — it won't be better!
Superhost
A well-maintained swimming pool is surrounded by lush greenery, with several lounge chairs arranged neatly on the grass. The area provides a serene atmosphere, complemented by various trees and flowering plants in the background.
Villa in Camaiore
4.93 out of 5 average rating, 45 reviews

La Dolce Vita - Tuscan experience

JonathanRating, 5 stars1 week ago
We had a wonderful stay, the house really felt like a home and was instantly relaxing. The whole booking and check in process was very straightforward and Giuseppe who met us to show us around the property and hand over the keys was very welcoming, kind and informative. The house has wonderfully peaceful location, with beautiful views. It has been furnished with excellent taste, and so adds to the feeling of being in a real home rather than a rental. The gardens and pool are delightful and evenings on the loggia will be remembered for a long time, we cant wait to return!
Top guest favorite
A tranquil pool area is highlighted by a clear blue pool flanked by sun loungers under white umbrellas. Lush greenery surrounds the property, with a charming farmhouse visible in the background, and inviting pathways guide guests through the scenic landscape.
Villa in San Ginese di Compito
4.99 out of 5 average rating, 129 reviews

Farmhouse , pool, 13 px. Lucca 10km

EduardoRating, 5 stars3 months ago
We had an amazing stay at Juri's beautiful villa in Tuscany! The place is super spacious, easily accommodating our group of 11, and it was spotless and very well maintained. Juri and his mom were incredible hosts—always responsive and ready to help whenever we needed anything. The location is also perfect for day trips to Florence, Pisa, and Lucca. If you're looking for a charming, well-kept and very clean villa with top-notch hospitality, this is the place. Highly recommend! Let me know if you'd like any tweaks!

Villa rentals with a pool

Guest favorite
A vibrant villa is set against a clear blue sky, surrounded by lush greenery. A private pool with lounge chairs and an umbrella invites relaxation. Stone steps lead from the pool area to the garden, enhancing the outdoor living experience.
Villa in Peccioli
4.99 out of 5 average rating, 70 reviews

Dream in Tuscany, Villa with pool

LauraRating, 5 stars1 month ago
Six of us spent a wonderful week at Vicky's villa to celebrate my husband's 60th birthday. The beautifully appointed house, the stunning views, and the swimming pool were all we had hoped for and more. Vicky is a five-star host. She welcomed us and even arranged to have a meal served upon our arrival. She generously helped us coordinate a catered birthday dinner at the villa. She shared interesting stories and lore from the area and made us feel very much at home. Before we left, she even took us on a tour of the magnificent Medici building under restoration on her property. From the villa, we headed out to Livorno, Pisa, Siena, and Florence, each a manageable day trip through the rolling Tuscan countryside. (Note: The final approach to the villa is over unpaved road; we were happy to have chosen an SUV for our rental.) We are left with great memories and many beautiful photographs of our stay in Peccioli. Thank you, Vicky!
Superhost
A large pool is shown, featuring clear turquoise water that reflects the blue sky above. Surrounding the pool are sunbathing areas with lounge chairs, and an ancient olive tree offers shade. Rustic buildings are faintly visible in the background, enhancing the serene landscape.
Villa in Rignano sull'Arno
4.95 out of 5 average rating, 138 reviews

Tuscan Dream Villa @ Rustic Elegance Near Florence

JessicaRating, 5 stars2 weeks ago
We enjoyed our stay at Il Casellino. The property is beautiful and peaceful. Super clean and very friendly host. Not a walkable location so driving a car is a must to come and go, nearest stores and restaurants are less than 10 minutes away but very worth it if you are looking for amazing panoramas. The pool area was better than the pictures!
Superhost
A serene outdoor area features a private swimming pool surrounded by lush greenery. Two lounge chairs and a small table are positioned beside the water, offering a relaxing space. The villa stands in the background, framed by trees and garden foliage.
Villa in Montopoli
4.83 out of 5 average rating, 58 reviews

Villa Belvedere beautiful view surrounded by greenery

RebekahRating, 5 stars1 week ago
Genka was the perfect host from start to finish, and the villa surpassed our expectations. Communication with Genka was great - he was quick to reply and gave us all the information we needed on the local area and beyond, even organising a taxi to take us to a local vineyard. The villa is beautiful and well-stocked with everything we needed. Genka had even thought to provide plenty of mosquito repellent for the house! Everything was clean and in good order and someone came each day to clean the pool (which we used a lot!). There are a couple of small shops and a supermarket close-by. The villa is situated on top of a hill, from which you can watch the sunrise in the morning and the sunset on the other side of the house in the evening. We will find it very hard not to book Genka's villa every year for our holiday! Grazie mille, Genka!
Guest favorite
Villa in San Gimignano
4.88 out of 5 average rating, 72 reviews

Lilium,delux farmhouse in the chianti hills

CharlotteRating, 5 stars2 weeks ago
We had a fantastic stay at Concetta's beautiful home! The house itself is gorgeous and traditionally Tuscan. It is also in the most incredible scenery and sitting outside and taking in the view was an absolute joy. However, by far the best thing about our stay was Concetta and her husband Paolo. They could not have done more to make us feel more at home and it honestly felt like we were part of the family while we were there (including making us the most incredible meal, which I would strongly recommend you do if you stay!) Their hospitality, helpfulness and warmth made it feel like a true escape and I could not recommend it more.
Top guest favorite
A serene view of the stone farmhouse is captured against a bright blue sky. Lush greenery surrounds the property, featuring olive trees and vibrant foliage. A sparkling swimming pool is situated in the foreground, reflecting the natural beauty of the landscape.
Villa in Sinalunga
5 out of 5 average rating, 44 reviews

The twigs

NatalieRating, 5 stars2 weeks ago
Sandrine’s Airbnb was by far the best accommodation we’ve ever experienced—a peaceful paradise nestled in the hills of Tuscany. What made it truly unforgettable, though, was the incredible generosity of our hosts. Sandrine welcomed us with a warm smile and thoughtfully provided delicious food and drink throughout our stay. She also shared wonderful recommendations for places to visit and things to see. It was a true blessing to meet such kindhearted and gracious people. 🙏
Guest favorite
A tranquil pool is surrounded by lush greenery, offering views of rolling hills in the distance. Colorful flowers frame the scene, adding a natural touch to the outdoor space. The pool features a ladder for easy access and a sparkling turquoise surface reflecting the sky.
Villa in Radda in Chianti
4.96 out of 5 average rating, 95 reviews

la Balza

LaurenRating, 5 stars5 days ago
We loved our time at La Balza - such a picturesque, peaceful and relaxing stay! Alessandro and his parents were a pleasure to deal with and answered all of my questions very quickly. They were very hospitable and accommodating. The area surrounding Radda in Chianti is absolutely beautiful and we loved the easy access to so many different cities and small villages. Would definitely recommend. A+
Guest favorite
Two lounge chairs are positioned beside a tranquil infinity pool, offering expansive views of lush green hills and valleys. Shade is provided by two large umbrellas, and a bright sky punctuated by soft clouds enhances the serene atmosphere.
Villa in Casciana Terme
4.95 out of 5 average rating, 66 reviews

Villa Le Rocche with pool, breathtaking view

UdayRating, 5 stars3 weeks ago
Incredible villa, meticulously maintained gardens and fruit trees, mesmerizing views and the gorgeous pool. Celebrated my father’s 70th birthday here with his kids and grandkids and we won’t forget it. Slice of heaven.
Superhost
A historic stone villa is set in a lush green landscape, surrounded by olive trees. An inviting swimming pool is visible in the foreground, lined with sun loungers. The villa's charming architecture is complemented by a clear blue sky with scattered clouds.
Villa in Civitella in Val di Chiana
4.92 out of 5 average rating, 25 reviews

Casa Quinti, let yourself be surprised by beauty.

ThomasRating, 5 stars1 week ago
We highly recommend Casa Quinti. Beautiful villa, surrounded by authentic Tuscan nature. Irene did a great job at welcoming us and giving us recommendations. We went with our three little kids all below 5 years old and they loved it, especially the pool. The house had everything we needed. Grazie Mille!

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